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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H29N5O3.ClH
Molecular Weight 520.023
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LECOZOTAN HYDROCHLORIDE

SMILES

Cl.C[C@H](CN(C(=O)C1=CC=C(C=C1)C#N)C2=CC=CC=N2)N3CCN(CC3)C4=C5OCCOC5=CC=C4

InChI

InChIKey=GXYZREDEYDFJPT-ZMBIFBSDSA-N
InChI=1S/C28H29N5O3.ClH/c1-21(31-13-15-32(16-14-31)24-5-4-6-25-27(24)36-18-17-35-25)20-33(26-7-2-3-12-30-26)28(34)23-10-8-22(19-29)9-11-23;/h2-12,21H,13-18,20H2,1H3;1H/t21-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C28H29N5O3
Molecular Weight 483.5616
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

LECOZOTAN, a benzodioxanylpiperazine derivative, is a selective serotonin 1A receptor antagonist. It was in development for the symptomatic treatment of cognitive deficits in Alzheimer's disease.

Approval Year

PubMed

PubMed

TitleDatePubMed
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
2005 May 19
Lecozotan (SRA-333): a selective serotonin 1A receptor antagonist that enhances the stimulated release of glutamate and acetylcholine in the hippocampus and possesses cognitive-enhancing properties.
2005 Sep
Progress update: Pharmacological treatment of Alzheimer's disease.
2007
A positron emission tomography study to assess binding of lecozotan, a novel 5-hydroxytryptamine-1A silent antagonist, to brain 5-HT1A receptors in healthy young and elderly subjects, and in patients with Alzheimer's disease.
2008 Jan
Bilobalide modulates serotonin-controlled behaviors in the nematode Caenorhabditis elegans.
2009 Jun 22
Safety, tolerability, pharmacokinetics and pharmacodynamics of ascending single and multiple doses of lecozotan in healthy young and elderly subjects.
2009 Mar
Drug development for Alzheimer's disease: recent progress.
2010 Dec
Acute lecozotan administration increases learning and memory in rats without affecting anxiety or behavioral depression.
2010 May
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:35:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:40 GMT 2023
Record UNII
23EDE20K1X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LECOZOTAN HYDROCHLORIDE
USAN  
USAN  
Official Name English
SRA-333
Code English
LECOZOTAN HCL
Common Name English
4-Cyano-N-[(2R)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]-N-(pyridin-2-yl)benzamide monohydrochloride
Systematic Name English
BENZAMIDE, 4-CYANO-N-((2R)-2-(4-(2,3-DIHYDRO-1,4-BENZODIOXIN-5-YL)-1-PIPERAZINYL)PROPYL)-N-2-PYRIDINYL-, MONOHYDROCHLORIDE
Common Name English
LECOZOTAN HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
Code System Code Type Description
FDA UNII
23EDE20K1X
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
USAN
PP-82
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
SMS_ID
300000044441
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
CAS
433282-68-9
Created by admin on Fri Dec 15 15:35:40 GMT 2023 , Edited by admin on Fri Dec 15 15:35:40 GMT 2023
PRIMARY
NCI_THESAURUS
C72813
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL372205
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID20195826
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
PUBCHEM
11156648
Created by admin on Fri Dec 15 15:35:41 GMT 2023 , Edited by admin on Fri Dec 15 15:35:41 GMT 2023
PRIMARY
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ACTIVE MOIETY